System Engineer

Prosper Solutions

Salary: $65,000–$75,000 annually, depending on qualifications and experience

Benefits: Health benefits and 401(k)

Location: Greater Boston / Saugus, MA area

Department: Technical Services / Command Center / Service Desk

Local candidates within 30 min of driving distance to the office only due to the onsite nature of the role and the need for timely office and client support.

Address: 999 Broadway, Suite #304, Saugus MA 01906

Prosper Solutions is a veteran-owned Managed Service Provider and Business Service Provider helping organizations build secure, reliable, and business-aligned technology environments.

We support nonprofit organizations, commercial businesses, municipalities, professional services firms, and other mission-driven organizations. Our services include IT support, cybersecurity, cloud management, infrastructure modernization, compliance readiness, and long-term technology planning.

Our team values ownership, accountability, clear communication, strong documentation, and doing the right thing for the client. We are looking for a technical professional who enjoys solving problems, supporting users, contributing to projects, and growing their skills.

The Tier 2 Systems Engineer / Service Desk Engineer combines day-to-day technical support with systems administration, monitoring, infrastructure support, project assistance, and documentation.

You will resolve support issues, handle escalations from frontline support, maintain client systems, and assist with technical deployments. You should be comfortable independently troubleshooting common issues, following established procedures, and escalating complex problems with clear documentation.

This is an opportunity for someone with at least two years of relevant IT experience who wants to grow across Microsoft cloud services, networking, cybersecurity, infrastructure, and automation.

• Provide remote and onsite technical support for client users, workstations, servers, cloud services, networks, and business applications.
• Troubleshoot Windows, macOS, Microsoft 365, hardware, software, email, VPN, printing, connectivity, and general user issues.
• Manage assigned tickets through our PSA platform, maintaining accurate notes, timely updates, and clear client communication.
• Resolve Tier 2 support issues and elevate advanced or high-impact problems to the appropriate engineering resources.
• Use RMM tools for remote support, endpoint management, monitoring, patching, and approved scripting tasks.
• Investigate endpoint, server, network, backup, and security alerts, following documented response and escalation procedures.
• Support Microsoft 365 environments, including Exchange Online, Teams, Teams Phone, SharePoint, One Drive, Entra , user accounts, licensing, and access permissions.
• Assist with Windows Server, Active Directory, Group Policy, DNS, DHCP, file servers, Azure, and hybrid cloud environments.
• Troubleshoot networking issues involving firewalls, switches, wireless networks, VPNs, and VLANs.
• Assist with endpoint protection, email security, MFA, identity and access management, and other security tools.
• Monitor backups and assist with recovery tasks using platforms such as Datto, Veeam, Slide, or similar technologies.
• Participate in client visits, hardware installations, migrations, onboarding, infrastructure upgrades, and project deployments.
• Support project engineers with implementation tasks, testing, documentation, and client communication.
• Create and maintain technical documentation, SOPs, client environment notes, checklists, diagrams, and knowledge base articles.
• Assist with ticket coordination, scheduling, client follow-up, and related operational tasks when needed.
• Participate in the on-call rotation after appropriate onboarding and training.
• Contribute ideas for process improvements, automation, and responsible use of AI-assisted workflows.

• At least two years of relevant "MSP" IT support, technical services, or systems administration experience in an MSP, IT service provider, internal IT department, or multi-client technical support environment.
• Strong troubleshooting ability across Windows desktops, Microsoft 365, basic networking, user support, and common business applications.
• Experience with a PSA or ticketing system such as HaloPSA, Connect Wise, Autotask, Service Now, Zendesk, or similar.
• Experience with an RMM platform such as Ninja One, Datto RMM, Connect Wise Automate, Kaseya,…